N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide

Base Information

• Chemical Name: N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide
• CAS No.: 75624-28-1
• Molecular Formula: C₁₉H₃₁N₇O₆
• Molecular Weight: 453.498

Synonyms:N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide

Chemical Property of N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide

There total 1 articles about N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

triethyl 1,3,5-triazine-2,4,6-tricarboxylate (898-22-6) → Nα-((tert-butyloxy)carbonyl)-Nβ-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide (75624-28-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 95 percent / dioxane / 21 h / 101 °C

2: 75 percent / CF₃SO₃H / CH₂Cl₂ / 13 h / 40 °C

3: NaBH₄ / ethanol / 15 h / 25 °C

4: 83 percent / MnO₂ / acetonitrile / 3 h / 82 °C

5: 98 percent / mol. sieves 4A / acetonitrile / 24 h / 25 °C

6: 1.) tin(II) trifluoromethanesulfonate, i-Pr₂NEt / 1.) THF, -20 deg C, 1 h, 2.) THF, from -78 deg C to 0 deg C, 12 h

7: 91 percent / Bu₃SnH, AIBN / benzene / 0.75 h / 80 °C

8: 80 percent / 16percent NH₃/EtOH / 1.5 h / 0 °C

With manganese(IV) oxide; sodium tetrahydroborate; tin(II) trifluoromethanesulfonate; 2,2'-azobis(isobutyronitrile); ethanol; trifluorormethanesulfonic acid; 4 A molecular sieve; ammonia; tri-n-butyl-tin hydride; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; ethanol; dichloromethane; acetonitrile; benzene;

DOI:10.1021/ja00092a012

Reference yield:

Nα-((tert-butyloxy)carbonyl)-Nβ-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide (75624-28-1) → C66H85N16O12S3(1+)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / LiOH / tetrahydrofuran; H₂O; methanol / 1 h / 0 °C

2: 68 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt / tetrahydrofuran; dimethylformamide / 55 h / 25 °C

3: 98 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 °C

4: 64 percent / DDC, HOBt, NaHCO₃ / dimethylformamide / 72 h / 25 °C

With lithium hydroxide; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2`,3`-dideoxycytidine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

Reference yield:

Nα-((tert-butyloxy)carbonyl)-Nβ-<1-amino-3(S)-(6-amino-4-(ethoxycarbonyl)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide (75624-28-1) → (2S,3R)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-amino)-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid (147911-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / LiOH / tetrahydrofuran; H₂O; methanol / 1 h / 0 °C

2: 68 percent / 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride, HOBt / tetrahydrofuran; dimethylformamide / 55 h / 25 °C

3: 98 percent / LiOH / tetrahydrofuran; methanol; H₂O / 1.5 h / 0 °C

With lithium hydroxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

upstream raw materials:

triethyl 1,3,5-triazine-2,4,6-tricarboxylate

Downstream raw materials:

(2S,3R)-2-({6-Amino-2-[(S)-1-((S)-2-tert-butoxycarbonylamino-2-carbamoyl-ethylamino)-2-carbamoyl-ethyl]-5-methyl-pyrimidine-4-carbonyl}-amino)-3-hydroxy-3-(1-trityl-1H-imidazol-4-yl)-propionic acid

N^α-((tert-butyloxy)carbonyl)-N^β-<1-amino-3(S)-(4-amino-6-(amido-N^im-(triphenylmethyl)-erythro-β-hydroxy-L-histydyl methyl ester)-5-methylpyrimidin-2-yl)propion-3-yl>-(S)-β-aminoalanine amide

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